Prev. Article Next Article Table of Contents

Letter

Tandem Conjugate Addition−Elimination for the Diastereoselective Synthesis of 4E-Alkenyl syn-1,3-Diols

Supporting Info

Delphine Rotulo-Sims and Joëlle Prunet*

Laboratoire de Synthse Organique, UMR CNRS 7652, Ecole Polytechnique, DCSO, F-91128 Palaiseau, France

Org. Lett., 2007, 9 (21), pp 4147–4150

DOI: 10.1021/ol701624y

Publication Date (Web): September 19, 2007

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, joelle.prunet@polytechnique.fr

Abstract

We have developed a tandem conjugate addition−elimination sequence for the diastereoselective synthesis of protected allylic syn-1,3-diols, starting from vinyl sulfones. The sulfonyl group was then reduced with sodium amalgam to furnish the E-olefin as the major isomer. This method was applied to the synthesis of a trisubstituted alkene modeling the C21−C25 fragment of Dolabelide C.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue October 11, 2007
Received July 11, 2007

Recommend & Share

Related Content

Dramatic Solvent Effect on the Diastereoselectivity of Michael Addition: Study toward the Synthesis of the ABC Ring System of Hexacyclinic AcidOrganic Letters
- Dramatic Solvent Effect on the Diastereoselectivity of Michael Addition: Study toward the Synthesis of the ABC Ring System of Hexacyclinic Acid
  Julie Toueg and Joëlle Prunet
  Organic Letters 2008 10 (1), pp 45–48
  Abstract: During our studies toward the synthesis of the ABC ring system of hexacyclinic acid, we have observed a dramatic influence of the solvent on both our key steps. The diastereoselectivity of the intermolecular Michael addition could be totally reversed by ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Total Synthesis of (−)-SerotobenineJournal of the American Chemical Society
- Total Synthesis of (−)-Serotobenine
  Yasuaki Koizumi, Hideki Kobayashi, Toshiyuki Wakimoto, Takumi Furuta, Tohru Fukuyama and Toshiyuki Kan
  Journal of the American Chemical Society 2008 130 (50), pp 16854–16855
  Abstract: The efficient total synthesis of (−)-serotobenine (1) has been achieved by constructing an optically active dihydrobenzofuran ring via a rhodium carbenoid mediated intramolecular C−H insertion reaction, which was developed by our group. Then the ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Synthesis and Structure of Mycolactone E Isolated from Frog MycobacteriumOrganic Letters
- Synthesis and Structure of Mycolactone E Isolated from Frog Mycobacterium
  Sylvain Aubry, Richard E. Lee, Engy A. Mahrous, Pam L. C. Small, Dia Beachboard and Yoshito Kishi
  Organic Letters 2008 10 (23), pp 5385–5388
  Abstract: The structure of mycolactone E, isolated from the frog pathogen Mycobacterium liflandii, was established via organic synthesis. Within the mycolactone family of metabolites, a structural variation has been seen only at the unsaturated fatty acid moiety ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF

Letter

Tandem Conjugate Addition−Elimination for the Diastereoselective Synthesis of 4E-Alkenyl syn-1,3-Diols

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Dramatic Solvent Effect on the Diastereoselectivity of Michael Addition: Study toward the Synthesis of the ABC Ring System of Hexacyclinic Acid

Total Synthesis of (−)-Serotobenine

Synthesis and Structure of Mycolactone E Isolated from Frog Mycobacterium

Other ACS content by these authors:

JOURNALS

BOOKS

MAGAZINE

COMMUNITIES

DIRECTORIES & DATABASES